CH312042A - Process for preparing a succinimide. - Google Patents
Process for preparing a succinimide.Info
- Publication number
- CH312042A CH312042A CH312042DA CH312042A CH 312042 A CH312042 A CH 312042A CH 312042D A CH312042D A CH 312042DA CH 312042 A CH312042 A CH 312042A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethylamine
- succinimide
- acid
- preparing
- dimethylsuccinic
- Prior art date
Links
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 title claims description 11
- 229960002317 succinimide Drugs 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- ACJPFLIEHGFXGP-UHFFFAOYSA-N 3,3-dimethyloxolane-2,5-dione Chemical compound CC1(C)CC(=O)OC1=O ACJPFLIEHGFXGP-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical group OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Description
Procédé de préparation d'une succinimide. L'invention se rapporte à un procédé de préparation d'une succinimide possédant une activité chimiothérapeutique, la N-éthyl-ëc,a- diméthylsuccinimide, de formule
EMI0001.0009
Selon l'invention, cette succinimide est pré parée en faisant réagir l'acide a,a-diméthyl- succin.ique ou l'anhydride a,
a-diméthylsuccini- que avec au moins un équivalent chimique d'éthylamine, et en chauffant le produit inter médiaire ainsi formé à une température com prise entre 100 et 350 C.
Pour l'exécution de la première partie (Iii procédé, il est avantageux, quoique non essen tiel, d'employer un solvant inerte tel que l'eau, un alcool aliphatique inférieur ou un mélange de tels alcools, l'éther, le benzène, le toluène ou semblables, pour faciliter la réaction de l'acide ou de l'anhydride avec l'éthylamine. Il est indiqué d'employer plusieurs équivalents d'éthylamine par équivalent d'acide ou d'an hydride a,
a-diméthylsucciniques. Les produits intermédiaires sont différents selon celle des deux matières premières susindiquées que l'on a employée, et aussi selon la quantité d'éthyl- amine utilisée.
Lorsqu'on emploie l'anhydride a;a-diméthylsuccinique avec un équivalent d'éthylamin.e, le produit intermédiaire est la semi-amide, tandis que si deux ou plus de deux équivalents d'éthylamine sont employés, le produit intermédiaire est le sel d'éthylamine de la semi-amide de l'acide a,a-diméthylsucci- nique. Dans le cas où l'on emploie l'acide a,:
a-diméthylsuccinique comme matière de dé part, le produit intermédiaire est le sel mono- ou di-éthylaminique de l'acide a,a-diméthyl- succinique. Ces produits intermédiaires peu vent être convertis en la succinimide désirée en les chauffant à une température comprise entre 100 et 350 C.
La température préférée pour cette conversion se trouve dans la région de 190 à 210 C, température à laquelle la réaction est complète au bout d'environ une heure.
Le produit obtenu par le procédé selon l'invention est une nouvelle substance ayant un point d'ébullition de 76-77 C sous 5 mm Hg et possède de précieuses propriétés théra peutiques et est particulièrement utile pour le traitement du type petit mal de l'épilepsie.
L'invention est illustrée par les exemples suivants <I>Exemple 1:</I> On ajoute graduellement 10 g d'acide a,a- diméthylsuccinique à 20 g d'éthylamine aqueuse et élimine ensuite l'eau et l'excès d'amine par distillation. La température du résidu est éle vée et maintenue à 200 C jusqu'à ce qu'il n'y ait plus dégagement d'éthylamine. On dis
tille le résidu dans le vide et obtient la N- éthyl-a, -diméthylsuccinimidecherchée; P. E. 76-77 C/5 mm. Rendement: 76 %.
<I>Exemple 2:</I> On ajoute graduellement 10 g d'anhydride a,a-diméthylsuccinique à 10 g d'éthylamine dans de l'éthanol; puis l'alcool et -'amine en excès sont éliminés par distillation. On chauffe le résidu à 210 C jusqu'à ce qu'il n'y ait plus dégagement d'éthylamine;
on le distille en suite dans le vide et l'on obtient la N-éthyl- a,a-diméthylsuceinimide cherchée; P. E. 76 à 77 C/5 mm. Rendement: 79 0/0.
Process for preparing a succinimide. The invention relates to a process for preparing a succinimide having chemotherapeutic activity, N-ethyl-ëc, α-dimethylsuccinimide, of formula
EMI0001.0009
According to the invention, this succinimide is prepared by reacting the α, α-dimethyl-succin.ique acid or the anhydride α,
a-dimethylsuccinic with at least one chemical equivalent of ethylamine, and heating the intermediate product thus formed to a temperature between 100 and 350 C.
For carrying out the first part (III process, it is advantageous, although not essential, to employ an inert solvent such as water, a lower aliphatic alcohol or a mixture of such alcohols, ether, benzene. , toluene or the like, to facilitate the reaction of the acid or anhydride with ethylamine. It is indicated to use several equivalents of ethylamine per equivalent of acid or anhydride a,
a-dimethylsuccinics. The intermediate products are different depending on which of the two above-mentioned raw materials is used, and also depending on the amount of ethylamine used.
When α; α-dimethylsuccinic anhydride is used with one equivalent of ethylamine, the intermediate is the half-amide, while if two or more equivalents of ethylamine are used, the intermediate is α, α-Dimethylsuccinic acid half-amide ethylamine salt. In the case where acid a is used:
α-Dimethylsuccinic As a starting material, the intermediate product is the mono- or di-ethylamine salt of α, α-dimethyl-succinic acid. These intermediates can be converted to the desired succinimide by heating them to a temperature between 100 and 350 C.
The preferred temperature for this conversion is in the region of 190-210 C, at which temperature the reaction is complete after about one hour.
The product obtained by the process according to the invention is a new substance having a boiling point of 76-77 C at 5 mm Hg and has valuable therapeutic properties and is particularly useful for the treatment of the mild illness type. epilepsy.
The invention is illustrated by the following examples <I> Example 1: </I> 10 g of α, α-dimethylsuccinic acid are gradually added to 20 g of aqueous ethylamine and then the water and excess d amine by distillation. The temperature of the residue is raised and maintained at 200 ° C. until there is no more evolution of ethylamine. We say
The residue is filtered off in vacuo and the desired N-ethyl-a, -dimethylsuccinimide is obtained; P. E. 76-77 C / 5 mm. Yield: 76%.
<I> Example 2: </I> 10 g of α, α-dimethylsuccinic anhydride is gradually added to 10 g of ethylamine in ethanol; then the excess alcohol and -'amine are removed by distillation. The residue is heated to 210 ° C. until there is no further evolution of ethylamine;
it is then distilled in vacuo and the desired N-ethyl-a, a-dimethylsuceinimide is obtained; P. E. 76 to 77 C / 5 mm. Yield: 79%.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US312042XA | 1952-02-26 | 1952-02-26 | |
| CH306792T | 1953-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH312042A true CH312042A (en) | 1955-12-15 |
Family
ID=25735202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH312042D CH312042A (en) | 1952-02-26 | 1953-02-07 | Process for preparing a succinimide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH312042A (en) |
-
1953
- 1953-02-07 CH CH312042D patent/CH312042A/en unknown
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